101-31-5 Usage
Description
L-Hyoscyamine, also known as Levorotatory Hyoscyamine, is a naturally occurring alkaloid with a 2S-configuration, structurally similar to atropine. It is derived from various solanaceous species, with one of the commercial sources being Egyptian henbane (Hyoscyamus muticus). L-Hyoscyamine exhibits inhibitory activity against cholinesterases and is characterized by its white to off-white solid appearance. L-Hyoscyamine is sparingly soluble in water, more soluble in ether or benzene, very soluble in chloroform, and freely soluble in alcohol. It is typically used as the sulfate or hydrobromide salt form, with the hydrobromide being preferred for its nondeliquescent nature and the salts being advantageous due to their water solubility.
Uses
Used in Pharmaceutical Industry:
L-Hyoscyamine is used as an anticholinergic and analgesic agent for the treatment of various conditions. Its anticholinergic properties help in reducing the effects of acetylcholine, a neurotransmitter, in the body, which can be beneficial in managing symptoms of certain disorders.
Used in Research Applications:
Biochem/physiol Actions
The 21st amino acid, selenocysteine (sec), is distinct from other amino acids because it lacks its own tRNA synthetase and is the only amino acid synthesized on its cognate tRNA. Synthesis of sec begins with acylation of tRNA(sec) (TRSP; MIM 165060) by seryl-tRNA synthetase (SARS; MIM 607529) to give ser-tRNA(sec), which is subsequently phosphorylated by O-phosphoseryl-tRNA kinase (PSTK; MIM 611310) to give O-phosphoseryl-tRNA(sec). SEPSECS catalyzes the final step of sec synthesis by converting O-phosphoseryl-tRNA(sec) to selenocysteinyl-tRNA(sec) using selenophosphate as the selenium donor (Palioura et al., 2009 [PubMed 19608919]).[supplied by OMIM]
Clinical Use
(L-Hyoscyamine)Hyoscyamine is used to treat disorders of the urinarytract more so than any other antispasmodic, although thereis no evidence that it has any advantages over the otherbelladonna preparations and the synthetic anticholinergics.It is used to treat spasms of the bladder and, in this manner,serves as a urinary stimulant. It is used together witha narcotic to counteract the spasm produced by the narcoticwhen the latter is used to relieve the pain of urethral colic.Hyoscyamine preparations are also used as antispasmodicsin the therapy of peptic ulcers.
Check Digit Verification of cas no
The CAS Registry Mumber 101-31-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 1 respectively; the second part has 2 digits, 3 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 101-31:
(5*1)+(4*0)+(3*1)+(2*3)+(1*1)=15
15 % 10 = 5
So 101-31-5 is a valid CAS Registry Number.
InChI:InChI=1/C17H23NO3/c1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13-,14+,15+,16-/m1/s1
101-31-5Relevant articles and documents
Absolute configuration of natural diastereoisomers of 6β- hydroxyhyoscyamine by vibrational circular dichroism
Munoz, Marcelo A.,Munoz, Orlando,Joseph-Nathan, Pedro
, p. 1335 - 1340 (2006)
The absolute configuration of the two natural diastereoisomers of 6β-hydroxyhyoscyamine has been determined using vibrational circular dichroism (VCD) spectroscopy. The predicted VCD and IR spectra of (3R,6R,2′S)-6β-hydroxyhyoscyamine (1) and (3S,6S,2′S)-6β- hydroxyhyoscyamine (2) were calculated using density functional theory (DFT) with the B3LYP functional and 6-31G(d) basis set and considering the eight lower energy conformations of each diastereoisomer. In both cases, the first four conformers showed the N-Me group in the syn orientation, permitting the formation of a hydrogen bond between the hydroxy group at the tropane ring and the tertiary nitrogen atom. In addition the eight conformers showed an intramolecular hydrogen bond between the hydroxy and carbonyl groups of the tropic ester moiety. The calculated IR spectra of both molecules showed good agreement with the experimental spectra, while comparison of the experimental and calculated VCD spectra showed that the absolute configuration of dextrorotatory 6β-hydroxyhyoscyamine is (3R,6R,2′S), while the levorotatory isomer is (3S,6S,2′S).
Tropic acid biosynthesis: The incorporation of (RS)-phenyl[2-18O,2-2H]lactate into littorine and hyoscyamine in Datura stramonium
Wong, Chi W.,Hamilton, John T. G.,O'Hagan, David,Robins, Richard J.
, p. 1045 - 1046 (1998)
The incorporation of oxygen-18 from (RS)-phenyl-[2-18O,2-2H]lactate into the tropane alkaloids littorine 1 and hyoscyamine 2 in Datura stramonium reveals that up to 29% of the oxygen-18 is lost during the transformation of 1 to 2.
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Schmidt et al.
, p. 1453,1454 (1967)
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Comparison of three S-β-CDs with different degrees of substitution for the chiral separation of 12 drugs in capillary electrophoresis
Wang, Zhaokun,Zhang, Qiongwen,Luo, Linda,Sun, Tiemin,Guo, Xingjie
, p. 558 - 565 (2017/08/26)
Three kinds of sulfated β-cyclodextrin (S-β-CD), including a single isomer, heptakis-6-sulfato-β-cyclodextrin (HS-β-CD), degree of substitution (DS) of 7, which was synthesized in our laboratory and another two commercialized randomly substituted mixtures, a sulfated β-cyclodextrin with DS of 7 to 11, as well as a highly sulfated-β-cyclodextrin with DS of 12 to 15, were used for the enantioresolution of 12 drugs (the β-blockers, phenethylamines, and anticholinergic agents) in capillary electrophoresis. The enantioseparation under varying concentrations of S-β-CD and background electrolyte pH were systematically investigated and compared. Based on the experimental results, the effect of the nature of S-β-CD and analyte structure on the enantioseparation is discussed.
